(a) Draw all stereoisomers of molecular formula C5H10Cl2 formed when (R)-2-chloropentane is heated with Cl2. (b) Assuming that products having different physical properties can be separated into fractions by some physical method (such as fractional distillation), how many different fractions would be obtained? (c) Which of these fractions would be optically active?

There are four dimethylcyclopropane isomers. (a) Write three-dimensional formulas for these isomers. (b) Which of the isomers are chiral? (c) If a mixture consisting of 1 mol of each of these isomers were subjected to simple gas chromatography, how many fractions would be obtained and which compounds would each fraction contain? (d) How many of these fractions would be optically active? tod o ors brie page 10 of 17

Draw the skeletal line-bond structure of (R)-4-isopropoxyoctane. Include a dash or wedge bond to indicate stereochemistry of substituents.

(S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A(C4H3O). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B(C,H140). Draw the structure of B.

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(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.